#72 - Rachel Sklar (TheLi.st)

Rachel Sklar built the most powerful women-in-tech network before “women’s communities” were trendy. In this episode of The Exit Whisperer, Carrie Kerpen sits down with Rachel, founder of The Li.st, to unpack the kind of exit founders never brag about — because it’s not a flashy SaaS story.

 

They get into the messy parts people skip: charging for community (hello, “pay to be her friend” headlines), why “perfect-fit” acquisitions die when you wait too long, what happens when the buyer’s lawyer kills the vibe, and why sometimes the smartest deal is the one that lets you sleep at night — even if it’s not the biggest number.

 

02:25 Meet Rachel Sklar: The Original Community Builder

03:05 Building The Li.st Before “Women’s Networks” Were Cool

06:09 Protecting Trust While Scaling

09:34 The Controversy

23:10 The Lessons Nobody Tells You

32:23 The “Perfect CEO” Idea (And The Plot Twist)

32:41 Startup Institute33:01 What The Li.st Could’ve Become

35:12 Pregnancy Changes The Timeline

36:30 COVID-19 Proves The Li.st’s Real Value

37:46 Handing Over The House You Built

52:30 Rachel’s Next Chapter After The Exit

58:54 What She’d Do Differently Now